One‐Pot Three‐Component Synthesis of 2‐Substituted 4‐Aminoquinazolines.

Rad‐Moghadam, Kurosh; Samavi, Laleh

doi:10.1002/chin.200651156

Cited by 3 publications

(5 citation statements)

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“…The synthesis starts from suitable amino-nicotinonitrile derivatives 37a – b (Scheme ). Construction of the pyrimidine moiety was achieved by heating with triethyl orthoformate as one-carbon fragment, yielding the pyrido[2,3- d ]pyrimidine and pyrido[3,2- d ]pyrimidine core structures 38a and 38b , respectively . The dimethoxyphenyl moiety is introduced via a Suzuki coupling, followed by reaction of the exocyclic amino group with cyclohexane carboxylic acid chloride, affording the desired final compounds 40a – b .…”

Section: Chemistrymentioning

confidence: 96%

“…After concentration under reduced pressure, the crude residue was treated with cyclohexanecarbonyl chloride according to general procedure E. The crude residue was purified by silicagel flash chromatography, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually ranging from 1/50 to 1/25), yielding the pure title compound as a white solid (40 mg, 32%). 1 5-Bromo-2-mercaptobenzonitrile (27). Into an oven-dried flask was added 5-bromo-2-fluorobenzonitrile (26, 400 mg, 2 mmol), Na 2 S (172 mg, 2.2 mmol), and DMF (2 mL) under nitrogen gas.…”

Section: N -( 5 -B R O M O B E N Z O [ B ] T H I O P H E N -3 -Y L )C...mentioning

confidence: 99%

“…These synthetic procedures allowed us to prepare a library around the isothiazolo [5,4-b]pyridine scaffold (see Tables 1, 2, and 3 for the exact structures that have been synthesized). 27 The dimethoxyphenyl moiety is introduced via a Suzuki coupling, followed by reaction of the exocyclic amino group with cyclohexane carboxylic acid chloride, affording the desired final compounds 40a−b.…”

Section: ■ Introductionmentioning

confidence: 99%

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Discovery of Dual Death-Associated Protein Related Apoptosis Inducing Protein Kinase 1 and 2 Inhibitors by a Scaffold Hopping Approach

et al. 2014

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DRAK2 emerged as a promising drug target for the treatment of autoimmune diseases and to prevent graft rejection after organ transplantation. Screening of a compound library in a DRAK2 binding assay led to the identification of an isothiazolo[5,4-b]pyridine derivative as a novel ligand for DRAK2, displaying a Kd value of 1.6 μM. Subsequent medicinal chemistry work led to the discovery of a thieno[2,3-b]pyridine derivative with strong DRAK2 binding affinity (Kd = 9 nM). Moreover, this compound also behaves as a functional inhibitor of DRAK2 enzymatic activity, displaying an IC50 value of 0.82 μM, although lacking selectivity, when tested against DRAK1. This paper describes for the first time functionally active dual DRAK1 and DRAK2 inhibitors that can be used as starting point for the synthesis of chemical tool compounds to study DRAK1 and DRAK2 biology, or they can be considered as hit compounds for hit-to-lead optimization campaigns in drug discovery programs.

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Section: Chemistrymentioning

confidence: 96%

Section: N -( 5 -B R O M O B E N Z O [ B ] T H I O P H E N -3 -Y L )C...mentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Discovery of Dual Death-Associated Protein Related Apoptosis Inducing Protein Kinase 1 and 2 Inhibitors by a Scaffold Hopping Approach

et al. 2014

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“…It should be noted that in this method the intramolecular addition of amines to the nitrile group occurs easily and in nearly neutral conditions; while under conventional condition, this reaction requires harsh conditions and strong Lewis acids [33]. Te advantages of this method are being one-pot, solvent free, operational simplicity, simple starting materials, mild condition, short reaction time, and high yields [34].…”

Section: 27mentioning

confidence: 99%

A Review on Current Synthetic Methods of 4-Aminoquinazoline Derivatives

Khabnadideh

Sadeghian

2022

Journal of Chemistry

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Quinazoline scaffold and its various derivatives, as an important category of heterocyclic compounds, have received much attention for the design and development of new drugs due to their various pharmacological properties like anticancer, anticonvulsant, antidepressant, antibacterial, antifungal, antioxidant, anti-HIV, antileishmanial, anticoccidial, antimalarial, anti-inflammatory, antileukemic, and antimutagenic. Among the various substituted quinazolines, 4-aminoquinazoline scaffold, as a privileged structure in medicinal chemistry, is present in many approved drugs and biologically active compounds. Furthermore, 4-aminoquinazoline derivatives are often applied as key intermediates in the preparation of bioactive compounds. The current review focuses on the key methods for the preparation of 4-aminoquinazoline derivatives, including the nucleophilic substitution reaction, metal-catalyzed approaches, microwave irradiation methods, cyclocondensation, and direct amination methods.

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“…Rad-Moghadam et al [106] synthesized various quinazolines 244 (five examples) under both MW irradiation and conventional heating conditions from a mixture of 2-aminobenzonitrile 242, orthoester 243, and ammonium acetate under solvent-free conditions (Scheme 68). MW method offers products in high yields (82-89%), in 5-7 min, whereas conventional method occurs in oil bath at 120˚C, in 30-80 min with 83-92% yield.…”

Section: Quinazolinementioning

confidence: 99%